Seco-pimarane diterpenoids and androstane steroids from an endophytic Nodulisporium fungus derived from Cyclosorus parasiticus.

Abstract

Five previously undescribed specialized metabolites, including three 9,11-seco-pimarane diterpenoids, nodulisporenones A-C, and two androstane steroids, nodulisporisterones A and B, together with previously described ergosterol derivatives, dankasterone A and demethylincisterol A3, were isolated from solid cultures of the endophytic fungus Nodulisporium sp. SC-J597. Their structures including absolute configurations were elucidated by extensive spectroscopic analysis and theoretical calculations of electronic circular dichroism spectra. Among them, nodulisporenones A and B are the first examples of seco-pimarane diterpenoids that is cyclized to form an unprecedented diterpenoid lactone scaffold and nodulisporisterones A and B represent the first normal C19 androstane steroids of fungal origin. Nodulisporisterone B exhibited potent inhibitory effect on the production of NO in LPS-stimulated RAW264.7 macrophages (IC50 = 2.95 μM). This compound, together with the two known ergosterol derivatives, also displayed cytotoxicity against A549, HeLa, HepG2 and MCF-7 cancer cell lines with IC50 values of 5.2-16.9 μM.

• Authors: Xiaoli Yang, Ping Wu, Jinghua Xue, Hanxiang Li, Xiaoyi Wei
• Journal: Phytochemistry (Phytochemistry) Vol. 210 Pg. 113679 (Jun 2023) ISSN: 1873-3700 [Electronic] England
• PMID: 37059288 (Publication Type: Journal Article)
• Copyright: Copyright © 2023 Elsevier Ltd. All rights reserved.

Chemical References

• Abietanes
• Steroids
• Diterpenes
• Androstanes
• Ergosterol

Topics

• Humans
• Abietanes (chemistry)
• Molecular Structure
• Steroids
• Diterpenes (chemistry)
• Androstanes
• Fungi
• Ergosterol